Literature DB >> 19271739

Vinylaluminum addition to sulfinimines (N-sulfinyl imines). Asymmetric synthesis of anti-alpha-alkyl beta-amino esters.

Franklin A Davis1, Hui Qiu, Minsoo Song, Narendra V Gaddiraju.   

Abstract

Addition of vinylaluminum NMO reagents to N-(p-toluenesufinyl)- and N-(2-methypropanesulfinyl)-derived sulfinimines gives N-sulfinyl aza-Morita-Baylis-Hillman products (dr = 7:1 to 12:1) that result from addition of the reagent from the least hindered direction. Hydrogenation of the aza-MBH adducts with a Rh(I) catalyst affords anti-alpha-substituted N-sulfinyl-beta-amino esters in good yield and high dr (10:1 to 21:1).

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Year:  2009        PMID： 19271739      PMCID： PMC2669707          DOI： 10.1021/jo9001504

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  18 in total

1.  Recent advances in the Baylis-Hillman reaction and applications.

Authors:  Deevi Basavaiah; Anumolu Jaganmohan Rao; Tummanapalli Satyanarayana
Journal:  Chem Rev       Date:  2003-03       Impact factor: 60.622

Review 2.  Application of alicyclic beta-amino acids in peptide chemistry.

Authors:  Ferenc Fülöp; Tamás A Martinek; Gábor K Tóth
Journal:  Chem Soc Rev       Date:  2006-01-19       Impact factor: 54.564

3.  Asymmetric thio-Michael/nucleophilic addition domino reaction with chiral N-sulfinimines.

Authors:  Akio Kamimura; Hidenori Okawa; Yuki Morisaki; Shingo Ishikawa; Hidemitsu Uno
Journal:  J Org Chem       Date:  2007-04-04       Impact factor: 4.354

Review 4.  Adventures in sulfur-nitrogen chemistry.

Authors:  Franklin A Davis
Journal:  J Org Chem       Date:  2006-11-24       Impact factor: 4.354

5.  Enantiomerically Pure alpha-Alkylidene beta-Amino Esters from Asymmetric Addition of Metal Dienolates to N-Sulfinylimines.

Authors:  J. L. García Ruano; I. Fernández; M. del Prado Catalina; J. A. Hermoso; J. Sanz-Aparicio; M. Martínez-Ripoll
Journal:  J Org Chem       Date:  1998-10-16       Impact factor: 4.354

6.  Highly selective alpha-acylvinyl anion additions to imines.

Authors:  Troy E Reynolds; Michael S Binkley; Karl A Scheidt
Journal:  Org Lett       Date:  2008-10-30       Impact factor: 6.005

7.  Enantioselective synthesis of alpha,beta-disubstituted-beta-amino acids.

Authors:  Mukund P Sibi; Narayanasamy Prabagaran; Sandeep G Ghorpade; Craig P Jasperse
Journal:  J Am Chem Soc       Date:  2003-10-01       Impact factor: 15.419

8.  Beta-peptidic peptidomimetics.

Authors:  Dieter Seebach; James Gardiner
Journal:  Acc Chem Res       Date:  2008-06-26       Impact factor: 22.384

9.  Asymmetric synthesis of beta-amino acid derivatives incorporating a broad range of substitution patterns by enolate additions to tert-butanesulfinyl imines.

Authors:  Tony P Tang; Jonathan A Ellman
Journal:  J Org Chem       Date:  2002-11-01       Impact factor: 4.354

10.  Vinylalumination for the synthesis of functionalized allyl alcohols, vinylepoxides, and alpha-alkylidene-beta-hydroxy-gamma-lactones.

Authors:  P Veeraraghavan Ramachandran; Michael T Rudd; Thomas E Burghardt; M Venkat Ram Reddy
Journal:  J Org Chem       Date:  2003-11-28       Impact factor: 4.354
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